DAT qVaults Ochem Exam 5 #5

[mario0923]

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http://forums.studentdoctor.net/attachment.php?attachmentid=19980&stc=1&d=1339725799

the question is what will be the product and I said no reaction

but according to datQvault the correct answer is benzoic acid

but the reagent is only permanganate and acid which will only react with alkene to make ketone/aldehyde when heated.

the reagent must be 1. permanganate, OH-, heat and 2. H3O+ in order to oxidize alkyl group in benzene.

am I wrong...??

 

[R1Guy]

http://forums.studentdoctor.net/attachment.php?attachmentid=19980&stc=1&d=1339725799

the question is what will be the product and I said no reaction

but according to datQvault the correct answer is benzoic acid

but the reagent is only permanganate and acid which will only react with alkene to make ketone/aldehyde when heated.

the reagent must be 1. permanganate, OH-, heat and 2. H3O+ in order to oxidize alkyl group in benzene.

am I wrong...??

The product will be benzoic acid. Chromic acid or potassium permanganate will oxidize R groups on the aromatic ring to carboxylic acids. Don't over analyze the way they show the reagents too much. For example, if they were listed the way you did, it will still oxidize to a carboxylic acid.

 

[Ari Rezaei]

Just to be more specific, this reaction will only work if there is a hydrogen on the benzylic carbon. If there is no hydrogen, no reaction will occur. So if tert butyl was attached, nothing would happen.

 

[mario0923]

thx guys
I hope I won't see any confusion in the real DAT...
hoping not to see both "no reaction" and benzoic acid in the answer choice...
I would have chosen benzoic acid if there was no "no reaction"
🙂